A highly debated topic among pro-wrestling fans is the greatest match of all time and what that means. Some consider the story being told, while others see it as purely the in-ring work. The honest answer to this question is that it is subjective, but that’s nowhere near as fun of an answer. In this blog post, I will discuss why Shawn Michaels vs. Undertaker at WrestleMania 26 is the greatest match ever.
This match was titled Streak vs. Career. Matches in pro-wrestling, let alone WWE, rarely get titles. This is a rare case and for a good reason. At this point, The Streak was a 17-year win streak at WrestleMania. No matter how beaten down, the Undertaker would always find a way to win at WrestleMania.
No one came as close as Shawn Michaels at WrestleMania 25 when he took Undertaker to his limit. This match blew fans away, with some thinking Shawn Michaels was about to end The Streak. In the end, Shawn made one mistake, costing him the match.
This is where the story begins as Shawn Michaels relapses to his former self, and the story blurs with reality. It is well-documented that Shawn had a colossal ego early in his career. He would cause conflict, and his character reflected that. Unfortunately, Shawn’s career was sidelined for four years after an injury in the 1998 Royal Rumble, ironically in a match against Taker.
This time away turned out to be incredibly helpful for Shawn. He developed a relationship with God and wrote a book about it years later. This changed him as a person, and that competitive ego was gone. It was no longer about the spotlight.
This storyline ends up bringing that version of Shawn Michaels back. After his loss at WrestleMania 25, he received an award for match of the year. Deep down, Shawn could not let go of his ego. He has done everything in his career except end The Streak. He challenges Undertaker to a rematch, and he says no.
This sends Shawn into a downward spiral, costing him the tag titles and betraying his best friend, Triple H. He started interfering with Undertaker’s matches and cost him the Heavyweight Championship.
This left Taker with no choice but to face him at WrestleMania 26, but under one condition: if Shawn lost, his career would be over. The match was set “Mr. WrestleMania” puts his career on the line to end Taker’s Mania win streak; it’s poetic.
This is all recapped in a beautifully made video package.
People were skeptical if this match could live up to WrestleMania 25, and in my opinion, it exceeded it.
Both wrestlers quickly went for their signatures and finishers. These are devastating moves designed to end matches and often do. Sometimes, they are overused. This is one of those instances where it was acceptable, as they are two of the best fighting for their legacy.
This match had one of the craziest near falls, truly making me think The Streak was over. Shawn Michaels does a backflip off the ring post to the announce table on Taker, gets him in the ring, and uses his finisher only for the two count.

The closing minutes of this math were truly something special. Shawn was entirely out of it, and Undertaker put him up for the tombstone, his finisher. He landed it, and Shawn kicked out at two. It was clear Shawn had nothing left.
Taker was about to do his signature rest in peace while waiting for him to get up but slowly stopped. He respected Shawn and almost pitied his situation. Shawn drags himself to his feet and slaps Taker, bringing out that ego one last time and essentially asking Undertaker to end it.
Undertaker hits him with one more tombstone, ending the match and Shawn’s career. After the match, Undertaker helped Shawn Michaels up. They embraced, and Taker left the ring. Shawn thanked the crowd as WrestleMania 26 went off the air.
Beyond storytelling, the in-ring work during the match was incredible. You come to expect this from talents of this level. You can put them in the ring with a broomstick, and they could make it work.
For me, good pro-wrestling is not spot fests. It’s good storytelling. It makes those incredible matches feel more remarkable when you understand the context of the moves being used. The why a punch is thrown is always more interesting than the punch.



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